Cefixime trihydrateProduct ingredient for Cefixime

Name
Cefixime trihydrate
Drug Entry
Cefixime

Bacteria possess a cell wall comprising a glycopeptide polymer commonly known as peptidoglycan, which is synthesized and remodelled through the action of a family of enzymes known as "penicillin-binding proteins" (PBPs).8 β-lactam antibiotics, including cephalosporins, are PBP inhibitors that, through inhibition of essential PBPs, result in impaired cell wall homeostasis, loss of cell integrity, and ultimately bacterial cell death.8,9,10 Cefixime is a broad-spectrum antibiotic and an orally-active third-generation semisynthetic cephalosporin.3,15,21 Cephalosporins are beta-lactam antibiotics and can be used to treat gram-positive and gram-negative bacterial infections which include conditions such as skin infections, resistant bacteria, and meningitis.12 Examples of third-generation cephalosporins are ceftriaxone, cefotaxime, and ceftazidime.12

Third-generation cephalosporins are often a first-line therapy against certain bacterial infections.17 However, cefixime is not recommended as a first-line of treatment for uncomplicated urogenital, anorectal, or pharyngeal gonorrhea because cefixime does not provide the same bactericidal effect as ceftriaxone.24,16 Generally, cefixime is used to treat uurinary tract infections, middle ear infections, pharyngitis, tonsillitis, exacerbations of chronic bronchitis, and uncomplicated gonorrhea.21 The beta-lactam ring of cefixime inhibits bacterial cell wall synthesis by binding to the penicillin-binding proteins which will then result in lysis.12,7,6 Specifically, cephalosporins inhibit penicillin-sensitive enzymes responsible for the final 3D structure of the bacterial cell wall which in turn inhibit bacterial cell wall peptidoglycan synthesis.19,20 Additionally, third-generation cephalosporins have been shown to have more stability in the presence of beta-lactamases compared to first- and second-generation cephalosporins.18 Cefixime was first approved in the United States in 1986.21

Accession Number
DBSALT001818
Structure
Synonyms
Not Available
UNII
97I1C92E55
CAS Number
125110-14-7
Weight
Average: 507.49
Monoisotopic: 507.072984244
Chemical Formula
C16H21N5O10S2
InChI Key
IPYWNMVPZOAFOQ-NABDTECSSA-N
InChI
InChI=1S/C16H15N5O7S2.3H2O/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7;;;/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27);3*1H2/b20-9-;;;/t10-,14-;;;/m1.../s1
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid trihydrate
SMILES
O.O.O.NC1=NC(=CS1)C(=N\OCC(O)=O)\C(=O)N[C@H]1[C@H]2SCC(C=C)=C(N2C1=O)C(O)=O
ChemSpider
4590586
Predicted Properties
PropertyValueSource
Water Solubility0.104 mg/mLALOGPS
logP0.25ALOGPS
logP-1.6Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.45Chemaxon
pKa (Strongest Basic)2.92Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area184.51 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity104.91 m3·mol-1Chemaxon
Polarizability41.59 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon